CN110022685A - For improving the water-soluble method of sesamin - Google Patents

For improving the water-soluble method of sesamin Download PDF

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Publication number
CN110022685A
CN110022685A CN201780065357.XA CN201780065357A CN110022685A CN 110022685 A CN110022685 A CN 110022685A CN 201780065357 A CN201780065357 A CN 201780065357A CN 110022685 A CN110022685 A CN 110022685A
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sesamin
water
poloxamer
surfactant
raising
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普拉亚·孔塔韦勒特
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Thai Center For Tissue Engineering And Stem Cell Excellence
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Thai Center For Tissue Engineering And Stem Cell Excellence
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/513—Organic macromolecular compounds; Dendrimers
    • A61K9/5161—Polysaccharides, e.g. alginate, chitosan, cellulose derivatives; Cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5192—Processes

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biomedical Technology (AREA)
  • Physics & Mathematics (AREA)
  • Molecular Biology (AREA)
  • Optics & Photonics (AREA)
  • Nanotechnology (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Biophysics (AREA)
  • Dispersion Chemistry (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Improve the water-soluble method of sesamin by generating the mixture of poloxamer and surfactant with sequence in the proper ratio, wherein the sesamin complex compound from the method be nanometer (nm) grade and water can be highly soluble in.After adding maltodextrin into the mixture with preferred speed and being subsequently dried or be freeze-dried the mixture, resulting sesamin powder is highly stable and can actively discharge its drug effect for a long time.

Description

For improving the water-soluble method of sesamin
Technical field
The present invention relates to chemistry and pharmaceutical science fields, in particular to by forming network with poloxamer and surfactant Polymeric composition improves the water-soluble method of sesamin.
Background technique
Sesamin, in chemistry also referred to as 5,5 '-(1S, 3aR, 4S, 6aR)-tetrahydro -1H, 3H- furans simultaneously [3,4-c] furan Mutter-Isosorbide-5-Nitrae-diyl is bis- (1,3- benzo two dislikes cyclopentadienyl), be belong to lignin may be present in one of sesame compound.It comes from Report that sesamin can control fatty acid metabolism (Umeda-Sawada, R., Fujiwara, Y., Abe, H.& in laboratory Seyama, Y. (2003) J.Nutr.Sci.Vitaminol. (" nutrition science and vitaminology magazine ") 49,442-446-10) With cholesterol (Kang YP, Wang NH, Jou HJ, Wang TA. (2006) J.Nutr. (" nutrition magazine ") (136 (5), 1270-1275).Furthermore it is known that it can also pre- anti-cancer (Harikumar KB, Sung B, Tharakan ST, Pandey MK, Joy B, Guha S, Krishnan S, Aggarwal BB, (2010) Mol.Cancer Research. (" grind by molecule cancer Study carefully ") 8 (5): 751-761) and protect neuron from caused by oxidation process stress (Hamada N., Fujita Y., Tanaka A., Naoi M., Nozawa Y. et al. (2009) J Neural Transm (" neural propagation magazine ") 116:841- 852)；In addition, it may also help in the reparation of bone inner cell (Wanachewin O., Klangjorhor J., Pothacharoen P.,Phitak T.,Loahapoonrungsee A.,Pruksakorn D.,Kongtawelert P.(2015) .J.Func.Food. (" functional food magazine ") 14:395-406).However, sesamin is with limited water-soluble and solvable In ethyl alcohol, and ethyl alcohol is only capable of with every milliliter 0.5 of edible solvent.
To solve the above-mentioned problems, it is used for continuous liquid carbon dioxide system to produce sesamin in a research report Nano particle (Arita T., Manabe N., Nakahara K.. (2012) Journal of Nanoparticle Research (" nano particle research magazine "), 14 (11), (2012): 1251)；However, this system still can generate it is high Cost and it also requires using specific equipment.
Currently, any not yet can effectively improve sesamin water-soluble (that is, improving sesamin solubility) and effectively control The system for making its release.Therefore, the present invention will be used together two kinds of drug substances to generate one group of sesamin complexing nano particle, These nano particles are water-soluble and can keep water-soluble for a long time.
Summary of the invention
The present invention relates to the complexings for realizing sesamin and two kinds of support substances (that is, complexing agent and surfactant) in order And micellization, to prevent the rupture of sesamin complex compound.The purpose of the present invention is for good and all improve sesamin water solubility, wherein institute The sesamin solution obtained can be at least 6-8 hours with slow release sesamin, are dissolved with solution with sesamin and capture and discharge The related any problem of sesamin, so as to improve medicinal effects or drug effect.
Detailed description of the invention
Fig. 1 is shown when every 200 microgram (μ g) sesamin is using 250 microlitres of (μ L) polysorbate80s, according to the present invention Sesamin complex compound size and size distribution an example.
Fig. 2 shows when every 200 μ g sesamin uses 250 μ L polysorbate80, sesamin according to the present invention is complexed One example of the zeta potential distribution of object.
Fig. 3 is shown when using 5mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to the present invention Sesamin complex compound size and size distribution an example.
Fig. 4 is shown when using 5mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to the present invention Sesamin complex compound zeta potential distribution an example.
Fig. 5 is shown when using 7.5mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this hair The size of bright sesamin complex compound and an example of size distribution.
Fig. 6 is shown when using 7.5mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this hair One example of the zeta potential distribution of bright sesamin complex compound.
Fig. 7 is shown when using 10mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this hair The size of bright sesamin complex compound and an example of size distribution.
Fig. 8 is shown when using 10mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this hair One example of the zeta potential distribution of bright sesamin complex compound.
Fig. 9 is shown when using 12.5mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this The size of the sesamin complex compound of invention and an example of size distribution.
Figure 10 is shown when using 12.5mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, sesamin One example of the zeta potential distribution of complex compound.
Figure 11 is shown when using 15mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this hair The size of bright sesamin complex compound and an example of size distribution.
Figure 12 is shown when using 15mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this hair One example of the zeta potential distribution of bright sesamin complex compound.
Figure 13 is shown when using 17.5mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this The size of the sesamin complex compound of invention and an example of size distribution.
Figure 14 is shown when using 17.5mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this One example of the zeta potential distribution of the sesamin complex compound of invention.
Figure 15 is shown when using 20mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this hair The size of bright sesamin complex compound and an example of size distribution.
Figure 16 is shown when using 20mg complex compound under every 200 μ g sesamin, 250 μ L polysorbate80, according to this hair One example of the zeta potential distribution of bright sesamin complex compound.
Figure 17 shows an example of table, and this table shows different amounts of poloxamers to sesamin nano particle The influence of size and size distribution.
Figure 18 shows an example of rate of release of the sesamin nano particle in 10mM HEPES solution (pH 7.4).
Specific embodiment
The raising water-soluble method of sesamin according to the present invention generally includes following steps: with the network based on poloxamer Mixture causes the generation of sesamin complex compound, and is wrapped in around the complex compound and generates micella for surfactant, In be dissolved under the appropraite condition as caused by two kinds of solution (i.e. sesamin and poloxamer) be self occur, to generate stabilization Mixture solution.
The method for preparing one group of sesamin complex compound specifically include using with the mass ratio of sesamin be 0.1-2:1-10, It is preferred that the complex solution of the poloxamer class of 0.5-2:1-10, and amount are not less than 200 microlitres of (μ of every 1 milligram of (mg) sesamin L), the preferred surfactant of 230-270 μ L.
The method of dissolution sesamin according to the present invention is the following steps are included: in organic solvent by sesamin dissolution, be somebody's turn to do Organic solvent is preferably chosen from chloroform, ethyl alcohol, methanol and DMSO, and the ratio of sesamin and solvent is 1-5:500-1,500 (quality Volume ratio), preferably 3:1,000 (mass volume ratio) simultaneously or sequentially prepares Poloxamer solution in water, wherein mooring Lip river The dosage of husky nurse is at least 1-10 times of sesamin weight in above-mentioned solution.Then, pool is added or is added dropwise into sesamin solution Luo Shamu solution, wherein poloxamer is preferably chosen from the derivative of any one in Poloxamer 127, poloxamer 80 or both Object, but most preferably poloxamer F127, with hand or equipment with preferred speed by solution mix until generate clarification or Transparent mixture.Then it adds into mixture or surfactant is added dropwise, which is preferably chosen from ion or non- Ionic surface active agent, but the non-ionic surface active being most preferably made of water-soluble poly sorbierite esters or polysorbate80 Agent, the amount of addition is not less than every 200 μ g sesamin 100-300 μ L, but preferably every 1mg sesamin and/or 1-15mg pool Lip river are husky Nurse 230-270 μ L, this will depend on the molecular weight of Poloxamer solution used.Then it is mixed with hand or equipment high-speed stirred Object, so that surfactant is distributed in entire mixture and generates white or muddy mixture solution.In addition, by 1-15 weight The maltodextrin for measuring % is added in mixture, and then mixed at high speed is to dissolve in the mixture the maltodextrin.So Afterwards by obtained mixture solution with 10,000-15,000 revs/min of speed, preferably with 12,500 revs/min of speed from Then the heart is freeze-dried or is lyophilized to remove any water and organic solvent, and obtain and have high stability and water-soluble final Sesamin product.
It has been found that this final sesamin product according to the present invention is high soluble when mixed with water；That is, 200 μ G sesamin can be completely dissolved by using 1mL water is no more than, and be characterized in that uniform white solution, not stratified also not have There is precipitating.
Above-mentioned increased solubility is caused by the initial complex compositions of sesamin molecule and poloxamer, then by making Surfactant molecule is wrapped in the micella for around the initial complex compositions and generating all size, these sizes depend on using In generate nanosized micelles poloxamer and surfactant type, and can by such as photon correlation spectrometer it The equipment of class measures, as shown in Fig. 1,3,5,7,9,11,13 and 15.Figure 17 is the various dosages from poloxamer to sesame The example of the value of the influence of the size and size distribution of plain nano particle.
When the acquired solution and water and organic dissolution of the one group of polysorbate80 that will include 100 μ L, 200 μ L and 300 μ L When being kept completely separate and evaporating and being freeze-dried under stress, resulting product is high soluble.It is surveyed when with 1 μ L to 5mL When examination, sesamin complex compound can be dissolved completely in the polysorbate80 mixture of 100 μ L or more, and wherein particle is big Small and particle surface zeta potential can be found in Fig. 1-16, and Figure 17 is shown in summarizing as a result.It has been found that in an example, using The polysorbate80 of 100 μ L can be such that the dissolution of sesame crude granule maximizes and have maximum stability, and can retain and be more than 70% sesamin.In a word, it is found that sesamin according to the present invention can be completely dissolved in water and can be with nanometer The form of grain saves or storage, which can be up to 7-8 hours with slow release sesamin, as described in Figure 18.
Although disclosing the present invention under the background of some embodiments and example, those skilled in the art will be managed Solution, the present invention will exceed specifically disclosed embodiment, extend to other alternate embodiments and/or purposes of the invention and its obvious Modification and equivalents.In addition, though several modifications of the invention have been shown specifically and have described, but based on this Open, those skilled in the art are readily apparent other modifications within the scope of the present invention.It is further envisioned that may be implemented to implement The specific features of example and the various combinations or sub-portfolio of aspect, and these combinations or sub-portfolio still fall within the scope of the present invention It is interior.It should be understood that the various features and aspect of the disclosed embodiments can be combined with each other or substitute, it is public to be formed The different mode for the invention opened.Therefore, it is intended that the range of present invention disclosed herein should not be by above-mentioned specifically disclosed implementation The limitation of example, and should only be determined by sufficiently reading the appended claims.

Claims (11)

1. a kind of complex compound and micellization by generating sesamin and complexing agent and surfactant is water-soluble to improve sesamin Property method, wherein the sesamin complex compound include the complexing agent based on poloxamer that mass ratio is 0.5-2:1-10 and Not less than the surfactant of every 200 μ L of 1mg sesamin.
2. the water-soluble method of raising sesamin according to claim 1, wherein being further added into the complex compound The maltodextrin of 1-15 weight %, for dry or freeze-drying or freeze-drying purpose.
3. the water-soluble method of raising sesamin according to claim 1, used in the poloxamer be selected from pool The derivative of Luo Shamu 127, poloxam 68 or Poloxamer 127 or poloxam 68.
4. the water-soluble method of raising sesamin according to claim 3, used in the poloxamer preferably It is poloxamer F127.
5. according to claim 1 or the water-soluble method of raising sesamin described in any one of 3, wherein the surfactant Selected from ionic surface active agent or nonionic surfactant.
6. the water-soluble method of raising sesamin according to claim 5, wherein the surfactant preferably by The nonionic surfactant of the water-soluble poly sorbierite esters composition of surfactant.
7. the water-soluble method of raising sesamin according to claim 6, wherein the polysorbate surfactant Preferably polysorbate80.
8. the water-soluble method of raising sesamin described in any one of -7 according to claim 1, used in the surface Activating agent is preferably every 1mg sesamin or 1-15mg poloxamer 230-270 μ L.
9. the water-soluble method of raising sesamin according to claim 1, wherein preparing the side of the sesamin complex compound Method includes:
-Step 1: sesamin is dissolved in organic solvent with the sesamin of 1-5:500-1,500 (mass volume ratio) and solvent ratio In；
-Step 2: poloxamer is prepared in water, and wherein the amount of poloxamer is the quality of the sesamin solution from step 1 1-10 times；
-Step 3: the Poloxamer solution is instilled in the sesamin solution, and is mixed them with hand or mixing apparatus Together, until the mixture becomes clarification；
-Step 4: surfactant is instilled in the mixture from step 3, and is mixed them with hand or mixing apparatus Together, the surfactant is disintegrated or is distributed in the mixture, until the mixture bleaches or muddiness；
-Step 5: the maltodextrin of 1-15% is added in the mixture and mixes them to dissolve the wheat Bud magma essence；And
-Step 6: the mixture of dry or freeze-drying or freeze-drying from step 5, to be removed from final sesamin product Water and organic solvent.
10. the water-soluble method of raising sesamin according to claim 9, wherein the organic solvent of step 1 is selected from Chloroform, methanol, ethyl alcohol, olive oil or DMSO.
11. the water-soluble method of raising sesamin according to claim 9, wherein by the mixture of step 6 with 10, 000-15,000 rev/min of speed centrifugation, then dry, freeze-drying or freeze-drying, from the final sesamin product Remove any water and organic solvent.
CN201780065357.XA 2017-02-14 2017-02-14 For improving the water-soluble method of sesamin Pending CN110022685A (en)

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Application publication date: 20190716